Acetone → 2-(6-Carboxy-2-cis-hexenyl)cyclopent-3-en-1-one

HRID 1448353Notes

Reaction equation

HRID 1448353 reaction equation
[OH:1][CH:2]1[CH2:6][CH:5]=[CH:4][CH:3]1/[CH:7]=[CH:8]\[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14].CC(C)=O.[Cr](O)(O)(=O)=O>S(=O)(=O)(O)O>[C:13]([CH2:12][CH2:11][CH2:10][CH2:9]/[CH:8]=[CH:7]\[CH:3]1[CH:4]=[CH:5][CH2:6][C:2]1=[O:1])([OH:15])=[O:14]

Participants

5

Reactant 3

HCID 180AcetoneHCID 24425Chromic AcidHCID 867329701-Hydroxy-2-(6-carboxy-2-cis-hexenyl)cyclopent-3-ene

Product 1

HCID 867329692-(6-Carboxy-2-cis-hexenyl)cyclopent-3-en-1-one

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 3.2 g. of 1-hydroxy-2-(6-carboxy-2-cis-hexenyl)cyclopent-3-ene (Example 55) in 60 ml. of reagent acetone is treated dropwise with a total of 6 ml. of 8 N chromic acid in sulfuric acid at 0° C. The oxidation is rather slow. The resulting mixture is dissolved in 200 ml. of water and the solution is extracted with six 50 ml. portions of ether. The combined ethereal extracts are dried over sodium sulfate and the solvent is evaporated at reduced pressure to yield the product as a yellow oil.

Workup

  1. customat 0° C
  2. dissolutionThe resulting mixture is dissolved in 200 ml
  3. extractionof water and the solution is extracted with six 50 ml
  4. dry with materialThe combined ethereal extracts are dried over sodium sulfate
  5. customthe solvent is evaporated at reduced pressure

Sources & evidence

ORD record
ord-9bc60c733fcb4ca4a0e9d3824953f202
Source dataset
uspto-grants-1979_12
Patent number
US04179451

Reaction notes

Loading…